Application of Grignard reagents to the synthesis of tertiary methylamines via resin-bound oxyiminium ions

The solid-phase synthesis of tertiary methylamines via the nucleophilic displacement of benzotriazole Mannich adducts with Grignard reagents using a hydroxylamine linker is described. The chemistry is exemplified by the synthesis of the MAO inhibitor α-methylpargyline. Also described is the synthesis of the analgesic Tramadol by an alternative one-pot solid-phase Mannich reaction.